Commands are responsible to build menu items for themselves. By default they build single item. But you can override method and generate multiple items.
Look for example at ClySwitchQueryScopeCommand>>#fillContextMenu:using:

It would be nice to have a complete 1:1 example to a more-complex world menu.
I see the value of using Commander, but it is (imho) order of magnitude more complex.

E.g., for a trivial method that creates a parent and a child entry

(aBuilder item: #Parent)
icon: #plus asIcon;
label: 'Parent';
parent: #MostUsedTools;
keyText: 'o, p';
action: [ self doParentStuff ].
(aBuilder item: #Child)
parent: #Parent;
label: 'Child';
icon: #minus asIcon;
keyText: 'o, c';
action: [ self doChildStuff ].

* I would need two classes, one for each command
* For each line of the builder a I need a separate method (shortcut, name, icon, ...)
* I need another class to represent the "parent" context (similar to CmdWorldMenuContext)
* I need to know to know how Commander work to even know what I am doing -- with the current setup it is obvious and people can just copy paste and be done.

I don't really think that it can be any simpler than is the current state, so any change would inevitably increase complexity. And with commander it feels like a lot of incidental complexity here.

Would it be possible to somehow generate commands on the fly? Some sort of "CmdPluggableCommand" that would be populated based on the current builder?

Peter